Homologxje of tropin and the process of producing same



an alcohol or UNITED STATES PATENT OFFICE.

EMIL MULLER. OF BASEL. SWITZERLAND. ASSIGNOR TO THE HOFFMANN-LA ROCHE CHEMIGAL WORKS, OF NEW YORK. N. Y.. A CORYORATION OF NEW YORK.

HOMOLdGUE OF TROPIN AND THE PROCESS OF YRODUCING SAME.

Nollmwing.

To all whom if may concern Be it known that I, Emmi MiiLLsn, a citizen of Switzerland, and a resident of Basel, Switzerland. have invented a certain new and useful Ilomologue of 'lropin and the Process of Producing Same, of which the following is a specification.

My invention relates in general to homo.- logues of tropin and in particular to that homologue which has the formula H NU and which 1 term homotropin. 'lropin (C H NO) has the following graphic formula:

I'lomolognes of tropin have heretofore never been recognized. I have discovered that by treating dihydrtianhyilroeegouinalkyl ester with sodium in a solution of absolute alcohol. l obtain homotropin II NO having the following graphic formula:

ciI -cu -cII -eu,on 2 5 l Nun en,

en u--en.

Ilomot-ropin is dillicultly soluble in petroleum ether: easily soluble in ether, benzol, water. it crystallizes from ligroin in long needles n'hieh melt at 85 'lhe homotropin hydrm-hlorid melts at .Zlt)" and is soluble in \\'ilt,(t'ul aleohol and insoluble in ether. The platimnn compound is very soluble in watch the gold eompound and the pierate ue dillienltly soluble. llomotropin rotates the plane of polarized light to the right; thus the plane of polarization will be turned to /a ,=22.51.

Ewannple.

Specification of Letters Patent.

Patented Sept. 7, 1920.

The reaction which takes place may be illustrated as follows:

tilled and fraetionized. Its boiling point is UH-I31 at 17mm.

to parts dihydroanliydroeegiminethylester, dissolved in 150 parts absolute alcohol, and at boiling temperature, is reduced by 2% parts sodium. The earboxyl group is thereby reduced to a primary alcohol group in aeeordanee with the following equation:

l lhydroanhydro- The solution is then aeidilied with con-.

rentrated hydroehlorie acid and the aleohol evaporated; the aeidulous solution remaining is then nentraliztal with potassium hydroxid and the homotropin produeed is washed out with ether. The ether solution is then dried with potassium hydroxid and the ether distilled oll'. yellow oil is obtained whieh after a time becomes stable and, by dissolving in ligroin and deerystallizing. a pure homotropin with a'melting point of 85 is obtained.

It is to he understood that l do not lilnit myself to the. precise details set forth but. that variations may he made without departing from my invention as set forth in the appended elaims.

l elaim:

l. homologue of tropin which may he formed by treating dihydf'oanhydroeegoninalkyl ester with sodium in a solution of absolute alcohol and is dillicultly soluble in potroleum ether and easily soluble in ether, henzol, alcohol or water, whirh :tullizvs from ligroiu in long needles which melt at 85 C. and rotates the plane of polarized light to the right, whose hydrochlorid melts at 210 C. and is soluble in water and alcohol and insoluble in other, and whose platinum compound and picrnte are difiicultly l0 soluble in water.

2. The process of producing homotropin comprising treating dih drounhydroecgoniuul liyl ester with :1 W1 uring agent in u solution of absolute alcohol.

3. The process of producing homotropin comprising treating dihydroanhydroecgoninethyl ester with sodium in a solution of absolute alcohol.

In testimony whereof I have hereunto set my hand.

EMIL MULLER. 

